7 Fresh Ways To Wear Dresses With Boots This Fall

fall dresses with boots
Photographed by Daniel Jackson, Vogue, October 2015 

Pairing a fabulous dress with a great pair of boots is a perennially reliable outfit formula for fall. There’s endless possibilities, depending on your own personal style of course. Slip into a cozy sweater dress or a ruffled prairie midi, and lace up in one of the season’s trendy boots like flat, mid-calf boots or chunky pull-ons. Or opt for a timeless silhouette like a knee high or lace-up combat. No matter the occasion, a dress and boot combo is an easy go-to for any fall activity, from a weekend upstate to a nice outdoor dinner.

Here, 7 chic ways to style fall dresses with boots to get you started.

Practical Prairie

Toughen up a romantic, frilled dress with a pair of lace-up boots. 

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Free People Rare Feeling pleated maxi dress

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Sam Edelman Garret combat platform boots

Can’t Believe It’s Not Butter

Melt into a turtleneck sweater dress and ultra-soft leather knee highs for maximum coziness. 

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Michael Michael Kors ribbed-knit turtleneck minidress

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By Far Steve 45 leather knee-high boots

Fall Into Winter 

These sweet snow boots will be sure to sell out long before the first frost. Snag them while you can, and pair them with a tiered babydoll. 

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Merlette Astell floralprint babydoll dress

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Ganni leather and linen boots

Case In Point

Make a subtly smooth statement in ultra-sharp ankle booties and a sleek pointed-collar shirt dress.

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Staud Cest Zipper Ponte maxi dress

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Manu Atelier duck boots

Match the Season

Channel fall in autumnal florals and classic brown leather.

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Banjanan Hana floral-print cotton dress

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J.Crew tall slouch Willa boots

Twice-as-Nice Knits

You can now literally dress in head-to-toe knits. 

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Telfar sweater tank dress

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Chloé Franne ribbed wool ankle boots

Rain Check

Pairing a pleated fall dress with short, waterproof boots has you ready for any occasion.

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Thebe Magugu knitted dress

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Bottega Veneta BV Puddle rain boots